Potassium Carbonate → HCID 10185215, compound

HRID 2250977Notes

Reaction equation

HRID 2250977 reaction equation
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C1C=C(C=CC=1)CBr.C[C:20]([NH:45]C(OC(C)(C)C)=O)([CH2:24][C:25]1[CH:30]=[C:29]([Br:31])[C:28]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)=[C:27]([Br:44])[CH:26]=1)[C:21]([OH:23])=[O:22]>CC(C)=O>[NH2:45][CH:20]([CH2:24][C:25]1[CH:26]=[C:27]([Br:44])[C:28]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:41])[F:43])[CH:35]=2)=[C:29]([Br:31])[CH:30]=1)[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 69203544HCID 69203544, compound

Product 1

HCID 10185215HCID 10185215, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of methyl-2-tert-butoxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl) propionate (0.20 g, 0.44 mmol), potassium carbonate (0.15 g, 1.1 mmol) and acetone (15 mL) was added 3-trifluormethyl benzylbromide (0.26 g, 1.1 mmol). The procedure followed was the same as described in Example 1, but the isolation on column chromatography of the intermediate methyl-2-tert-butoxycarbonylamino-3-[3,5-dibromo-4-(3-trifluormethylbenzyloxy)phenyl]propionic acid was not done. Purification of the final residue by HPLC, using the same conditions as described in Example 1(b), gave 20 mg (9%) of 2-amino-3-[3,5-dibromo-4-(3-trifluormethylbenzyloxy)phenyl]propionic acid. LC-MS (electrospray): m/z 498 (M+1).

Workup

  1. customPurification of the final residue by HPLC

Sources & evidence

ORD record
ord-d5fba71e597d4c07a3a5cb23737f8c48
Source dataset
uspto-grants-2008_01
Patent number
US07319096B2

Reaction notes

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